Well, now I have a dilemma. I own TitS on PSP. Physical copy. I want to link a playthrough from 1 to 2. I am also planning on buying a Vita in 2014. My options:

-Buy 2nd Chapter on PSN, play it on my PSP. Move it to Vita later when I eventually get one. -Buy TitS on Steam, replay it, buy 2nd Chapter on Steam, play that. -Buy a TitS on Vita, replay it, buy 2nd Chapter on Vita, play that.

Right now leaning towards option 1, honestly. Option 3 will probably happen eventually, but a year or two down the line when I want to replay all of them.

What order are they supposed to be played through?With this one, will they all be on Steam?

The first TitS will be on Steam later this year. The second one will be on PSN and Steam in 2014.

The earlier Legend of Heroes games are in a weird order in their Western releases and my recommendation... is not to play any of them. The PSP versions of LoH 1 through 3 (which I think are actually 3 through 5?) are bad. Just play Trails in the Sky, as it's the first chapter in a new saga, and then wait for the second chapter to come out next year.